Add changelog about sentry tracking

changelog.d/7602.sdk

@@ -0,0 +1 @@
+Add sentry tracking around send message task.

matrix-sdk-android/src/main/java/org/matrix/android/sdk/api/extensions/MetricsExtensions.kt

@@ -25,14 +25,17 @@ import kotlin.contracts.contract
 /**
  * Executes the given [block] while measuring the transaction.
  *
+ * @param T type of the output from [block]
  * @param block Action/Task to be executed within this span.
+ *
+ * @return Output of the [block()]
  */
 @OptIn(ExperimentalContracts::class)
-inline fun List<MetricPlugin>.measureMetric(block: () -> Unit) {
+inline fun <T> List<MetricPlugin>.measureTransaction(block: () -> T): T {
     contract {
         callsInPlace(block, InvocationKind.EXACTLY_ONCE)
     }
-    try {
+    return try {
         this.forEach { plugin -> plugin.startTransaction() } // Start the transaction.
         block()
     } catch (throwable: Throwable) {
@@ -46,16 +49,19 @@ inline fun List<MetricPlugin>.measureMetric(block: () -> Unit) {
 /**
  * Executes the given [block] while measuring a span.
  *
+ * @param T type of the output from [block]
  * @param operation Name of the new span.
  * @param description Description of the new span.
  * @param block Action/Task to be executed within this span.
+ *
+ * @return Output of the [block]
  */
 @OptIn(ExperimentalContracts::class)
-inline fun List<SpannableMetricPlugin>.measureSpan(operation: String, description: String, block: () -> Unit) {
+inline fun <T> List<SpannableMetricPlugin>.measureSpan(operation: String, description: String, block: () -> T): T {
     contract {
         callsInPlace(block, InvocationKind.EXACTLY_ONCE)
     }
-    try {
+    return try {
         this.forEach { plugin -> plugin.startSpan(operation, description) } // Start the transaction.
         block()
     } catch (throwable: Throwable) {

matrix-sdk-android/src/main/java/org/matrix/android/sdk/api/metrics/SendServiceMetricPlugin.kt

@@ -0,0 +1,32 @@
+/*
+ * Copyright 2022 The Matrix.org Foundation C.I.C.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ * http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.matrix.android.sdk.api.metrics
+
+import org.matrix.android.sdk.api.logger.LoggerTag
+import timber.log.Timber
+
+private val loggerTag = LoggerTag("SendServiceMetricPlugin", LoggerTag.CRYPTO)
+
+/**
+ * An spannable metric plugin for tracking send message, events or command task.
+ */
+interface SendServiceMetricPlugin : SpannableMetricPlugin {
+
+    override fun logTransaction(message: String?) {
+        Timber.tag(loggerTag.value).v("## sendService() : $message")
+    }
+}

matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/DeviceListManager.kt

@@ -22,7 +22,7 @@ import org.matrix.android.sdk.api.MatrixConfiguration
 import org.matrix.android.sdk.api.MatrixCoroutineDispatchers
 import org.matrix.android.sdk.api.MatrixPatterns
 import org.matrix.android.sdk.api.auth.data.Credentials
-import org.matrix.android.sdk.api.extensions.measureMetric
+import org.matrix.android.sdk.api.extensions.measureTransaction
 import org.matrix.android.sdk.api.metrics.DownloadDeviceKeysMetricsPlugin
 import org.matrix.android.sdk.api.session.crypto.crosssigning.DeviceTrustLevel
 import org.matrix.android.sdk.api.session.crypto.model.CryptoDeviceInfo
@@ -355,7 +355,7 @@ internal class DeviceListManager @Inject constructor(
         val relevantPlugins = metricPlugins.filterIsInstance<DownloadDeviceKeysMetricsPlugin>()
 
         val response: KeysQueryResponse
-        relevantPlugins.measureMetric {
+        relevantPlugins.measureTransaction {
             response = try {
                 downloadKeysForUsersTask.execute(params)
             } catch (throwable: Throwable) {

matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/tasks/RedactEventTask.kt

@@ -15,6 +15,9 @@
  */
 package org.matrix.android.sdk.internal.crypto.tasks
 
+import org.matrix.android.sdk.api.MatrixConfiguration
+import org.matrix.android.sdk.api.extensions.measureSpan
+import org.matrix.android.sdk.api.metrics.SendServiceMetricPlugin
 import org.matrix.android.sdk.internal.network.GlobalErrorReceiver
 import org.matrix.android.sdk.internal.network.executeRequest
 import org.matrix.android.sdk.internal.session.room.RoomAPI
@@ -32,18 +35,23 @@ internal interface RedactEventTask : Task<RedactEventTask.Params, String> {
 
 internal class DefaultRedactEventTask @Inject constructor(
         private val roomAPI: RoomAPI,
-        private val globalErrorReceiver: GlobalErrorReceiver
+        private val globalErrorReceiver: GlobalErrorReceiver,
+        matrixConfiguration: MatrixConfiguration
 ) : RedactEventTask {
 
+    private val relevantPlugins = matrixConfiguration.metricPlugins.filterIsInstance<SendServiceMetricPlugin>()
+
     override suspend fun execute(params: RedactEventTask.Params): String {
-        val response = executeRequest(globalErrorReceiver) {
-            roomAPI.redactEvent(
-                    txId = params.txID,
-                    roomId = params.roomId,
-                    eventId = params.eventId,
-                    reason = if (params.reason == null) emptyMap() else mapOf("reason" to params.reason)
-            )
+        relevantPlugins.measureSpan("send_service.execute_redact_event_task", "Execute redact event task") {
+            val response = executeRequest(globalErrorReceiver) {
+                roomAPI.redactEvent(
+                        txId = params.txID,
+                        roomId = params.roomId,
+                        eventId = params.eventId,
+                        reason = if (params.reason == null) emptyMap() else mapOf("reason" to params.reason)
+                )
+            }
+            return response.eventId
         }
-        return response.eventId
     }
 }

matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/tasks/SendEventTask.kt

@@ -15,6 +15,9 @@
  */
 package org.matrix.android.sdk.internal.crypto.tasks
 
+import org.matrix.android.sdk.api.MatrixConfiguration
+import org.matrix.android.sdk.api.extensions.measureSpan
+import org.matrix.android.sdk.api.metrics.SendServiceMetricPlugin
 import org.matrix.android.sdk.api.session.events.model.Event
 import org.matrix.android.sdk.api.session.room.model.localecho.RoomLocalEcho
 import org.matrix.android.sdk.api.session.room.send.SendState
@@ -41,47 +44,58 @@ internal class DefaultSendEventTask @Inject constructor(
         private val loadRoomMembersTask: LoadRoomMembersTask,
         private val createRoomFromLocalRoomTask: CreateRoomFromLocalRoomTask,
         private val roomAPI: RoomAPI,
-        private val globalErrorReceiver: GlobalErrorReceiver
+        private val globalErrorReceiver: GlobalErrorReceiver,
+        matrixConfiguration: MatrixConfiguration
 ) : SendEventTask {
 
+    private val relevantPlugins = matrixConfiguration.metricPlugins.filterIsInstance<SendServiceMetricPlugin>()
+
     override suspend fun execute(params: SendEventTask.Params): String {
-        try {
-            if (params.event.isLocalRoomEvent) {
-                return createRoomAndSendEvent(params)
-            }
-
-            // Make sure to load all members in the room before sending the event.
-            params.event.roomId
-                    ?.takeIf { params.encrypt }
-                    ?.let { roomId ->
-                        try {
-                            loadRoomMembersTask.execute(LoadRoomMembersTask.Params(roomId))
-                        } catch (failure: Throwable) {
-                            // send any way?
-                            // the result is that some users won't probably be able to decrypt :/
-                            Timber.w(failure, "SendEvent: failed to load members in room ${params.event.roomId}")
-                        }
+        relevantPlugins.measureSpan("send_service.execute_send_event_task", "Execute send event task") {
+            try {
+                if (params.event.isLocalRoomEvent) {
+                    return relevantPlugins.measureSpan("send_service.create_room_send_event", "Create room and send event") {
+                        createRoomAndSendEvent(params)
                     }
+                }
 
-            val event = handleEncryption(params)
-            val localId = event.eventId!!
-            localEchoRepository.updateSendState(localId, params.event.roomId, SendState.SENDING)
-            val response = executeRequest(globalErrorReceiver) {
-                roomAPI.send(
-                        localId,
-                        roomId = event.roomId ?: "",
-                        content = event.content,
-                        eventType = event.type ?: ""
-                )
-            }
-            localEchoRepository.updateSendState(localId, params.event.roomId, SendState.SENT)
-            return response.eventId.also {
-                Timber.d("Event: $it just sent in ${params.event.roomId}")
-            }
-        } catch (e: Throwable) {
+                // Make sure to load all members in the room before sending the event.
+                relevantPlugins.measureSpan("send_service.load_all_members", "Load all members of room") {
+                    params.event.roomId
+                            ?.takeIf { params.encrypt }
+                            ?.let { roomId ->
+                                try {
+                                    loadRoomMembersTask.execute(LoadRoomMembersTask.Params(roomId))
+                                } catch (failure: Throwable) {
+                                    // send any way?
+                                    // the result is that some users won't probably be able to decrypt :/
+                                    Timber.w(failure, "SendEvent: failed to load members in room ${params.event.roomId}")
+                                }
+                            }
+                }
+
+                val event = handleEncryption(params)
+                val localId = event.eventId!!
+                localEchoRepository.updateSendState(localId, params.event.roomId, SendState.SENDING)
+                relevantPlugins.measureSpan("send_service.room_send_event", "Send event in room") {
+                    val response = executeRequest(globalErrorReceiver) {
+                        roomAPI.send(
+                                localId,
+                                roomId = event.roomId ?: "",
+                                content = event.content,
+                                eventType = event.type ?: ""
+                        )
+                    }
+                    localEchoRepository.updateSendState(localId, params.event.roomId, SendState.SENT)
+                    return response.eventId.also {
+                        Timber.d("Event: $it just sent in ${params.event.roomId}")
+                    }
+                }
+            } catch (e: Throwable) {
 //            localEchoRepository.updateSendState(params.event.eventId!!, SendState.UNDELIVERED)
-            Timber.w(e, "Unable to send the Event")
-            throw e
+                Timber.w(e, "Unable to send the Event")
+                throw e
+            }
         }
     }
 
@@ -93,16 +107,18 @@ internal class DefaultSendEventTask @Inject constructor(
 
     @Throws
     private suspend fun handleEncryption(params: SendEventTask.Params): Event {
-        if (params.encrypt && !params.event.isEncrypted()) {
-            return encryptEventTask.execute(
-                    EncryptEventTask.Params(
-                            params.event.roomId ?: "",
-                            params.event,
-                            listOf("m.relates_to")
-                    )
-            )
+        relevantPlugins.measureSpan("send_service.encrypt_event", "Encrypt event") {
+            if (params.encrypt && !params.event.isEncrypted()) {
+                return encryptEventTask.execute(
+                        EncryptEventTask.Params(
+                                params.event.roomId ?: "",
+                                params.event,
+                                listOf("m.relates_to")
+                        )
+                )
+            }
+            return params.event
         }
-        return params.event
     }
 
     private val Event.isLocalRoomEvent

matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/session/room/send/DefaultSendService.kt

@@ -25,7 +25,11 @@ import dagger.assisted.Assisted
 import dagger.assisted.AssistedFactory
 import dagger.assisted.AssistedInject
 import kotlinx.coroutines.launch
+import org.matrix.android.sdk.api.MatrixConfiguration
 import org.matrix.android.sdk.api.MatrixUrls.isMxcUrl
+import org.matrix.android.sdk.api.extensions.measureSpan
+import org.matrix.android.sdk.api.extensions.measureTransaction
+import org.matrix.android.sdk.api.metrics.SendServiceMetricPlugin
 import org.matrix.android.sdk.api.session.content.ContentAttachmentData
 import org.matrix.android.sdk.api.session.events.model.Content
 import org.matrix.android.sdk.api.session.events.model.Event
@@ -73,9 +77,12 @@ internal class DefaultSendService @AssistedInject constructor(
         private val taskExecutor: TaskExecutor,
         private val localEchoRepository: LocalEchoRepository,
         private val eventSenderProcessor: EventSenderProcessor,
-        private val cancelSendTracker: CancelSendTracker
+        private val cancelSendTracker: CancelSendTracker,
+        matrixConfiguration: MatrixConfiguration,
 ) : SendService {
 
+    private val relevantPlugins = matrixConfiguration.metricPlugins.filterIsInstance<SendServiceMetricPlugin>()
+
     @AssistedFactory
     interface Factory {
         fun create(roomId: String): DefaultSendService
@@ -84,21 +91,45 @@ internal class DefaultSendService @AssistedInject constructor(
     private val workerFutureListenerExecutor = Executors.newSingleThreadExecutor()
 
     override fun sendEvent(eventType: String, content: JsonDict?): Cancelable {
-        return localEchoEventFactory.createEvent(roomId, eventType, content)
-                .also { createLocalEcho(it) }
-                .let { sendEvent(it) }
+        return relevantPlugins.measureTransaction {
+            relevantPlugins.measureSpan("send_service.create_event", "Create local event") {
+                localEchoEventFactory.createEvent(roomId, eventType, content)
+            }.also {
+                relevantPlugins.measureSpan("send_service.create_local_echo", "Create local echo") {
+                    createLocalEcho(it)
+                }
+            }.let {
+                relevantPlugins.measureSpan("send_service.send_event", "Send event") { sendEvent(it) }
+            }
+        }
     }
 
     override fun sendTextMessage(text: CharSequence, msgType: String, autoMarkdown: Boolean, additionalContent: Content?): Cancelable {
-        return localEchoEventFactory.createTextEvent(roomId, msgType, text, autoMarkdown, additionalContent)
-                .also { createLocalEcho(it) }
-                .let { sendEvent(it) }
+        return relevantPlugins.measureTransaction {
+            relevantPlugins.measureSpan("send_service.create_text_event", "Create local text event") {
+                localEchoEventFactory.createTextEvent(roomId, msgType, text, autoMarkdown, additionalContent)
+            }.also {
+                relevantPlugins.measureSpan("send_service.create_local_echo", "Create local echo") {
+                    createLocalEcho(it)
+                }
+            }.let {
+                relevantPlugins.measureSpan("send_service.send_event", "Send event") { sendEvent(it) }
+            }
+        }
     }
 
     override fun sendFormattedTextMessage(text: String, formattedText: String, msgType: String, additionalContent: Content?): Cancelable {
-        return localEchoEventFactory.createFormattedTextEvent(roomId, TextContent(text, formattedText), msgType, additionalContent)
-                .also { createLocalEcho(it) }
-                .let { sendEvent(it) }
+        return relevantPlugins.measureTransaction {
+            relevantPlugins.measureSpan("send_service.create_formatted_text_event", "Create local formatted text event") {
+                localEchoEventFactory.createFormattedTextEvent(roomId, TextContent(text, formattedText), msgType, additionalContent)
+            }.also {
+                relevantPlugins.measureSpan("send_service.create_local_echo", "Create local echo") {
+                    createLocalEcho(it)
+                }
+            }.let {
+                relevantPlugins.measureSpan("send_service.send_event", "Send event") { sendEvent(it) }
+            }
+        }
     }
 
     override fun sendQuotedTextMessage(
@@ -109,35 +140,67 @@ internal class DefaultSendService @AssistedInject constructor(
             rootThreadEventId: String?,
             additionalContent: Content?,
     ): Cancelable {
-        return localEchoEventFactory.createQuotedTextEvent(
-                roomId = roomId,
-                quotedEvent = quotedEvent,
-                text = text,
-                formattedText = formattedText,
-                autoMarkdown = autoMarkdown,
-                rootThreadEventId = rootThreadEventId,
-                additionalContent = additionalContent,
-        )
-                .also { createLocalEcho(it) }
-                .let { sendEvent(it) }
+        return relevantPlugins.measureTransaction {
+            relevantPlugins.measureSpan("send_service.create_quoted_text_event", "Create local quoted text event") {
+                localEchoEventFactory.createQuotedTextEvent(
+                        roomId = roomId,
+                        quotedEvent = quotedEvent,
+                        text = text,
+                        formattedText = formattedText,
+                        autoMarkdown = autoMarkdown,
+                        rootThreadEventId = rootThreadEventId,
+                        additionalContent = additionalContent,
+                )
+            }.also {
+                relevantPlugins.measureSpan("send_service.create_local_echo", "Create local echo") {
+                    createLocalEcho(it)
+                }
+            }.let {
+                relevantPlugins.measureSpan("send_service.send_event", "Send event") { sendEvent(it) }
+            }
+        }
     }
 
     override fun sendPoll(pollType: PollType, question: String, options: List<String>, additionalContent: Content?): Cancelable {
-        return localEchoEventFactory.createPollEvent(roomId, pollType, question, options, additionalContent)
-                .also { createLocalEcho(it) }
-                .let { sendEvent(it) }
+        return relevantPlugins.measureTransaction {
+            relevantPlugins.measureSpan("send_service.create_poll", "Create local poll event") {
+                localEchoEventFactory.createPollEvent(roomId, pollType, question, options, additionalContent)
+            }.also {
+                relevantPlugins.measureSpan("send_service.create_local_echo", "Create local echo") {
+                    createLocalEcho(it)
+                }
+            }.let {
+                relevantPlugins.measureSpan("send_service.send_event", "Send event") { sendEvent(it) }
+            }
+        }
     }
 
     override fun voteToPoll(pollEventId: String, answerId: String, additionalContent: Content?): Cancelable {
-        return localEchoEventFactory.createPollReplyEvent(roomId, pollEventId, answerId, additionalContent)
-                .also { createLocalEcho(it) }
-                .let { sendEvent(it) }
+        return relevantPlugins.measureTransaction {
+            relevantPlugins.measureSpan("send_service.reply_to_poll", "Create local reply poll event") {
+                localEchoEventFactory.createPollReplyEvent(roomId, pollEventId, answerId, additionalContent)
+            }.also {
+                relevantPlugins.measureSpan("send_service.create_local_echo", "Create local echo") {
+                    createLocalEcho(it)
+                }
+            }.let {
+                relevantPlugins.measureSpan("send_service.send_event", "Send event") { sendEvent(it) }
+            }
+        }
     }
 
     override fun endPoll(pollEventId: String, additionalContent: Content?): Cancelable {
-        return localEchoEventFactory.createEndPollEvent(roomId, pollEventId, additionalContent)
-                .also { createLocalEcho(it) }
-                .let { sendEvent(it) }
+        return relevantPlugins.measureTransaction {
+            relevantPlugins.measureSpan("send_service.end_poll", "Create local end poll event") {
+                localEchoEventFactory.createEndPollEvent(roomId, pollEventId, additionalContent)
+            }.also {
+                relevantPlugins.measureSpan("send_service.create_local_echo", "Create local echo") {
+                    createLocalEcho(it)
+                }
+            }.let {
+                relevantPlugins.measureSpan("send_service.send_event", "Send event") { sendEvent(it) }
+            }
+        }
     }
 
     override fun redactEvent(event: Event, reason: String?, additionalContent: Content?): Cancelable {
@@ -148,11 +211,13 @@ internal class DefaultSendService @AssistedInject constructor(
     }
 
     override fun resendTextMessage(localEcho: TimelineEvent): Cancelable {
-        if (localEcho.root.isTextMessage() && localEcho.root.sendState.hasFailed()) {
-            localEchoRepository.updateSendState(localEcho.eventId, roomId, SendState.UNSENT)
-            return sendEvent(localEcho.root)
+        relevantPlugins.measureTransaction {
+            if (localEcho.root.isTextMessage() && localEcho.root.sendState.hasFailed()) {
+                localEchoRepository.updateSendState(localEcho.eventId, roomId, SendState.UNSENT)
+                return relevantPlugins.measureSpan("send_service.resend_text_event", "Resend text message") { sendEvent(localEcho.root) }
+            }
+            return NoOpCancellable
         }
-        return NoOpCancellable
     }
 
     override fun resendMediaMessage(localEcho: TimelineEvent): Cancelable {
@@ -163,8 +228,10 @@ internal class DefaultSendService @AssistedInject constructor(
             val url = messageContent.getFileUrl() ?: return NoOpCancellable
             if (url.isMxcUrl()) {
                 // We need to resend only the message as the attachment is ok
-                localEchoRepository.updateSendState(localEcho.eventId, roomId, SendState.UNSENT)
-                return sendEvent(localEcho.root)
+                return relevantPlugins.measureTransaction {
+                    localEchoRepository.updateSendState(localEcho.eventId, roomId, SendState.UNSENT)
+                    relevantPlugins.measureSpan("send_service.resend_media_message", "Resend media message") { sendEvent(localEcho.root) }
+                }
             }
 
             // we need to resend the media

matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/session/room/send/queue/EventSenderProcessorCoroutine.kt

@@ -21,10 +21,13 @@ import kotlinx.coroutines.Dispatchers
 import kotlinx.coroutines.delay
 import kotlinx.coroutines.launch
 import kotlinx.coroutines.withContext
+import org.matrix.android.sdk.api.MatrixConfiguration
 import org.matrix.android.sdk.api.auth.data.SessionParams
+import org.matrix.android.sdk.api.extensions.measureTransaction
 import org.matrix.android.sdk.api.failure.Failure
 import org.matrix.android.sdk.api.failure.getRetryDelay
 import org.matrix.android.sdk.api.failure.isLimitExceededError
+import org.matrix.android.sdk.api.metrics.SendServiceMetricPlugin
 import org.matrix.android.sdk.api.session.Session
 import org.matrix.android.sdk.api.session.events.model.Event
 import org.matrix.android.sdk.api.util.Cancelable
@@ -58,11 +61,14 @@ internal class EventSenderProcessorCoroutine @Inject constructor(
         private val sessionParams: SessionParams,
         private val queuedTaskFactory: QueuedTaskFactory,
         private val taskExecutor: TaskExecutor,
-        private val memento: QueueMemento
+        private val memento: QueueMemento,
+        matrixConfiguration: MatrixConfiguration,
 ) : EventSenderProcessor {
 
     private val waitForNetworkSequencer = SemaphoreCoroutineSequencer()
 
+    private val relevantPlugins = matrixConfiguration.metricPlugins.filterIsInstance<SendServiceMetricPlugin>()
+
     /**
      * sequencers use QueuedTask.queueIdentifier as key.
      */
@@ -137,33 +143,35 @@ internal class EventSenderProcessorCoroutine @Inject constructor(
     }
 
     private suspend fun executeTask(task: QueuedTask) {
-        try {
-            if (task.isCancelled()) {
-                Timber.v("## $task has been cancelled, try next task")
-                return
-            }
-            task.waitForNetwork()
-            task.execute()
-        } catch (exception: Throwable) {
-            when {
-                exception is IOException || exception is Failure.NetworkConnection -> {
-                    canReachServer.set(false)
-                    task.markAsFailedOrRetry(exception, 0)
-                }
-                (exception.isLimitExceededError()) -> {
-                    task.markAsFailedOrRetry(exception, exception.getRetryDelay(3_000))
-                }
-                exception is CancellationException -> {
+        relevantPlugins.measureTransaction {
+            try {
+                if (task.isCancelled()) {
                     Timber.v("## $task has been cancelled, try next task")
+                    return
                 }
-                else -> {
-                    Timber.v("## un-retryable error for $task, try next task")
-                    // this task is in error, check next one?
-                    task.onTaskFailed()
+                task.waitForNetwork()
+                task.execute()
+            } catch (exception: Throwable) {
+                when {
+                    exception is IOException || exception is Failure.NetworkConnection -> {
+                        canReachServer.set(false)
+                        task.markAsFailedOrRetry(exception, 0)
+                    }
+                    (exception.isLimitExceededError()) -> {
+                        task.markAsFailedOrRetry(exception, exception.getRetryDelay(3_000))
+                    }
+                    exception is CancellationException -> {
+                        Timber.v("## $task has been cancelled, try next task")
+                    }
+                    else -> {
+                        Timber.v("## un-retryable error for $task, try next task")
+                        // this task is in error, check next one?
+                        task.onTaskFailed()
+                    }
                 }
             }
+            markAsFinished(task)
         }
-        markAsFinished(task)
     }
 
     private suspend fun QueuedTask.markAsFailedOrRetry(failure: Throwable, retryDelay: Long) {

matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/session/sync/SyncResponseHandler.kt

@@ -19,8 +19,8 @@ package org.matrix.android.sdk.internal.session.sync
 import com.zhuinden.monarchy.Monarchy
 import io.realm.Realm
 import org.matrix.android.sdk.api.MatrixConfiguration
-import org.matrix.android.sdk.api.extensions.measureMetric
 import org.matrix.android.sdk.api.extensions.measureSpan
+import org.matrix.android.sdk.api.extensions.measureTransaction
 import org.matrix.android.sdk.api.metrics.SyncDurationMetricPlugin
 import org.matrix.android.sdk.api.session.pushrules.PushRuleService
 import org.matrix.android.sdk.api.session.pushrules.RuleScope
@@ -71,7 +71,7 @@ internal class SyncResponseHandler @Inject constructor(
         val isInitialSync = fromToken == null
         Timber.v("Start handling sync, is InitialSync: $isInitialSync")
 
-        relevantPlugins.measureMetric {
+        relevantPlugins.measureTransaction {
             startCryptoService(isInitialSync)
 
             // Handle the to device events before the room ones

vector/src/main/java/im/vector/app/features/analytics/metrics/VectorPlugins.kt

@@ -17,6 +17,7 @@
 package im.vector.app.features.analytics.metrics
 
 import im.vector.app.features.analytics.metrics.sentry.SentryDownloadDeviceKeysMetrics
+import im.vector.app.features.analytics.metrics.sentry.SentrySendServiceMetrics
 import im.vector.app.features.analytics.metrics.sentry.SentrySyncDurationMetrics
 import org.matrix.android.sdk.api.metrics.MetricPlugin
 import javax.inject.Inject
@@ -29,9 +30,10 @@ import javax.inject.Singleton
 data class VectorPlugins @Inject constructor(
         val sentryDownloadDeviceKeysMetrics: SentryDownloadDeviceKeysMetrics,
         val sentrySyncDurationMetrics: SentrySyncDurationMetrics,
+        val sentrySendServiceMetrics: SentrySendServiceMetrics
 ) {
     /**
      * Returns [List] of all [MetricPlugin] hold by this class.
      */
-    fun plugins(): List<MetricPlugin> = listOf(sentryDownloadDeviceKeysMetrics, sentrySyncDurationMetrics)
+    fun plugins(): List<MetricPlugin> = listOf(sentryDownloadDeviceKeysMetrics, sentrySyncDurationMetrics, sentrySendServiceMetrics)
 }

vector/src/main/java/im/vector/app/features/analytics/metrics/sentry/SentrySendServiceMetrics.kt

@@ -0,0 +1,91 @@
+/*
+ * Copyright (c) 2022 New Vector Ltd
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package im.vector.app.features.analytics.metrics.sentry
+
+import io.sentry.ISpan
+import io.sentry.ITransaction
+import io.sentry.Sentry
+import io.sentry.SpanStatus
+import org.matrix.android.sdk.api.metrics.SendServiceMetricPlugin
+import java.util.EmptyStackException
+import java.util.Stack
+import javax.inject.Inject
+
+/**
+ * Sentry based implementation of SyncDurationMetricPlugin.
+ */
+class SentrySendServiceMetrics @Inject constructor() : SendServiceMetricPlugin {
+    private var transaction: ITransaction? = null
+
+    // Stacks to keep spans in LIFO order.
+    private var spans: Stack<ISpan> = Stack()
+
+    /**
+     * Starts the span for a sub-task.
+     *
+     * @param operation Name of the new span.
+     * @param description Description of the new span.
+     *
+     * @throws IllegalStateException if this is called without starting a transaction ie. `measureSpan` must be called within `measureMetric`.
+     */
+    override fun startSpan(operation: String, description: String) {
+        if (Sentry.isEnabled()) {
+            val span = Sentry.getSpan() ?: transaction
+            span?.let {
+                val innerSpan = it.startChild(operation, description)
+                spans.push(innerSpan)
+                logTransaction("Sentry span started: operation=[$operation], description=[$description]")
+            }
+        }
+    }
+
+    override fun finishSpan() {
+        try {
+            spans.pop()
+        } catch (e: EmptyStackException) {
+            null
+        }?.finish()
+        logTransaction("Sentry span finished")
+    }
+
+    override fun startTransaction() {
+        if (Sentry.isEnabled()) {
+            transaction = Sentry.startTransaction("SendService", "action.handle", true)
+            logTransaction("Sentry transaction started")
+        }
+    }
+
+    override fun finishTransaction() {
+        transaction?.finish()
+        logTransaction("Sentry transaction finished")
+    }
+
+    override fun onError(throwable: Throwable) {
+        try {
+            spans.peek()
+        } catch (e: EmptyStackException) {
+            null
+        }?.apply {
+            this.throwable = throwable
+            this.status = SpanStatus.INTERNAL_ERROR
+        } ?: transaction?.apply {
+            this.throwable = throwable
+            this.status = SpanStatus.INTERNAL_ERROR
+        }
+        logTransaction("Sentry transaction encountered error ${throwable.message}")
+    }
+}

vector/src/main/java/im/vector/app/features/analytics/metrics/sentry/SentrySyncDurationMetrics.kt

@@ -44,10 +44,12 @@ class SentrySyncDurationMetrics @Inject constructor() : SyncDurationMetricPlugin
      */
     override fun startSpan(operation: String, description: String) {
         if (Sentry.isEnabled()) {
-            val span = Sentry.getSpan() ?: throw IllegalStateException("measureSpan block must be called within measureMetric")
-            val innerSpan = span.startChild(operation, description)
-            spans.push(innerSpan)
-            logTransaction("Sentry span started: operation=[$operation], description=[$description]")
+            val span = Sentry.getSpan()
+            span?.let {
+                val innerSpan = it.startChild(operation, description)
+                spans.push(innerSpan)
+                logTransaction("Sentry span started: operation=[$operation], description=[$description]")
+            }
         }
     }